Manufacture of certain aldehydes.



1 are particu GEORGESDARZENS,

PATENT OFFICE.

OF PARIS, FRANCE.

MANUFACTURE OF CERTAIN AL DEHYDES.

Specification of Letters Patent.

Patented Sept. 4, 1906.

Application filed October 6,1904. Serial No. 227.472. (Specimena) To all whom it may concern:

Be it known that I, GEORGES DARZENS, of Paris, France, have invented a new and useful Manufacture of Certain Aldehydes and Intermediate Products, which invention is fully set forth in the following specification.

This invention relates to a manufacture of aldehydes by decomposing substituted oxyacrylio acids of formula o on oozo.n.. R

These aldeh des, which are very odoriferous, l arly a licable to perfumery, confectionery, and lil e purposes.

The manufacture consists, essentially, in condensing a fatty or aromatic ketone or generally a compound containing a CO group in itsmolecule with an ester of chloro-bromo or iodO-acetic acid in presence of sodium, so

dium ethylate, or any other alkaline condensing agent.

The ester, which'is formed according to the reaction o.H..o3 R! is then saponified by any usual process, and the acid obtained is decomposed either by merely raising the temperature or by distil ling under reduced pressure or in any other suitable manner.

The same result may be attained by con densing a compound of the form R-CO-R with other derivatives of glycollic acid.

Example I: A mixture of eight hundred and fifty grams of methylnonyl ketone and six hundred and twenty grams of ethyl chloracetate is treated with a solution of one hundred and twenty grams of sodium in two liters of absolute alcohol. After these materials have been in contact for some hours the mass is treated with water and the oil decanted and distilled in a vacuum. A condensation proiduct boiling at to centigrade un er sixteen millimeters pressure,

' limeters having a specific gravity of 0.836 at 0 centigrade, having a refractive index of 1.4245 for the D line at 28 centigrade, is thus isolated. The ester thus obtained is saponified and then distilled in a vacuum. It readily yields 'methylnonylacetaldchyde, boiling at 119 to 122 under sixteen millimeters pressure and giving a semicarbazone melting at 85 centigrade.

Example II: A mixture of two hundred and fifty grams of paratolylmethyl ketone and two hundred and forty grams of ethyl chloracetate is treated with a solution of forty-five grams of sodium in a liter of absolute alcohol. The product is a liquid boiling at 160 to 164 centigrade under sixteen milressure. When saponified and decom ose it yields paramethylhydratropic aldeliyde boiling at 107 to 108 centigrade under nineteen millimeters pressure. and giving a semicarbazone melting at 159 to 160 centigrade.

Example III: A mixture of two hundred and fift grams of benz lacetone and two hundre and ten grams of eth l chloracetate is treated with a solution of orty grams of sodium in a liter of absolute alcohol. The condensation product is a liquid boiling at to centi rade under sixteen millimeters pressure, which when saponified and decomposed yields methylphenylbutylic aldehyde boiling at 129 to 130 centigrade under nineteen millimeters pressure and giving a semicarbazone melting at 70 to 7 2. centigrade.

Having now particularly described and ascertained the nature of my said invention and in what manner the same is to be performed, I declare that What I claim is- 1. The process of making aldehydes, consisting. in condensing a body containing a CO group with an ester of a halogen derivative ofa atty acid, and transforming the resultant product into an aldehyde.

2. The process of making aldehydes, consisting in condensing a body containing a CO group with ethylmonochloracetic ester, and

transforming the resultant product into an aldehyde.

3. An aldehyde, methylnon lacetaldehyde derived from condensation o methylnonylketon with ethylmonohalogenaceticester, be-

ng an odoiiferol'is substance, having a boil- In witness whereof I have hereunto signed ng-point of 119 to 122 centigrade under my name, this 27th day of September, 1904, V ;ixteen millimeters pressure, having a spein the presence of two subscribing witnesses. 1o

zifie gravity of 0.836 at 0 centigrade, having GEORGES DARZENS. i refraction index of 1.4245 for the D line at Witnesses: 28 centigrade, and forming a semicarbezone JULEs ARMENGAUD, J eune w'hose melting-point is 85 centigradefi RENI ARMENGAUD. 

